# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_160448
_audit_block_doi                 10.5517/ccdc.csd.cc1mwlcg
_database_code_depnum_ccdc_archive 'CCDC 1516066'
_audit_update_record             
;
2016-11-10 deposited with the CCDC.
2016-12-12 downloaded from the CCDC.
;
_audit_creation_date             2016-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 F3 N2'
_chemical_formula_sum            'C14 H9 F3 N2'
_chemical_formula_weight         262.23
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   11.5964(5)
_cell_length_b                   11.5964(5)
_cell_length_c                   17.7913(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2392.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1861
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.6070
_cell_measurement_theta_min      3.8480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5592
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.332
_diffrn_reflns_theta_max         25.332
_diffrn_reflns_theta_min         2.886
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     63.00  94.00   1.00    4.50    --   18.81 178.00-180.00   31
  2  ω     -4.00  78.00   1.00    4.50    --   18.81  19.00-150.00   82
  3  ω    -36.00  -7.00   1.00    4.50    --  -19.74  37.00 -11.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0550206000
_diffrn_orient_matrix_UB_12      -0.0267263000
_diffrn_orient_matrix_UB_13      0.0005057000
_diffrn_orient_matrix_UB_21      -0.0233497000
_diffrn_orient_matrix_UB_22      -0.0488259000
_diffrn_orient_matrix_UB_23      -0.0185226000
_diffrn_orient_matrix_UB_31      0.0130556000
_diffrn_orient_matrix_UB_32      0.0252983000
_diffrn_orient_matrix_UB_33      -0.0353075000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1619
_reflns_number_total             2178
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 480 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0618
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0896P)²+0.6073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1667
_refine_ls_wR_factor_ref         0.1864
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5774(4) 0.5049(5) 0.3288(2) 0.1099(17) Uani 1 1 d . . . . .
F2 F 0.6700(4) 0.6470(4) 0.3748(2) 0.0923(13) Uani 1 1 d . . . . .
F3 F 0.7607(4) 0.5064(4) 0.32749(18) 0.0882(13) Uani 1 1 d . . . . .
N1 N 0.8572(4) 0.5687(4) 0.4913(2) 0.0533(11) Uani 1 1 d . . . . .
N2 N 0.8586(4) 0.4765(4) 0.6011(2) 0.0581(12) Uani 1 1 d . . . . .
H2 H 0.8815 0.4555 0.6450 0.070 Uiso 1 1 calc R . . . .
C1 C 1.0412(6) 0.7233(5) 0.5454(3) 0.0628(16) Uani 1 1 d . . . . .
H1 H 0.9966 0.7496 0.5055 0.075 Uiso 1 1 calc R . . . .
C2 C 1.1334(6) 0.7871(6) 0.5695(3) 0.0676(17) Uani 1 1 d . . . . .
H2A H 1.1515 0.8559 0.5454 0.081 Uiso 1 1 calc R . . . .
C3 C 1.1982(5) 0.7513(6) 0.6280(3) 0.0696(17) Uani 1 1 d . . . . .
H3 H 1.2591 0.7966 0.6448 0.083 Uiso 1 1 calc R . . . .
C4 C 1.1748(5) 0.6484(6) 0.6626(4) 0.0715(18) Uani 1 1 d . . . . .
H4 H 1.2215 0.6228 0.7017 0.086 Uiso 1 1 calc R . . . .
C5 C 1.0810(5) 0.5819(6) 0.6394(3) 0.0649(16) Uani 1 1 d . . . . .
H5 H 1.0636 0.5129 0.6635 0.078 Uiso 1 1 calc R . . . .
C6 C 1.0143(5) 0.6205(5) 0.5798(3) 0.0509(13) Uani 1 1 d . . . . .
C7 C 0.9096(5) 0.5546(5) 0.5564(2) 0.0491(13) Uani 1 1 d . . . . .
C8 C 0.7624(4) 0.4954(5) 0.4957(3) 0.0508(12) Uani 1 1 d . . . . .
C9 C 0.7616(5) 0.4358(5) 0.5633(3) 0.0539(13) Uani 1 1 d . . . . .
C10 C 0.6780(6) 0.3585(5) 0.5835(3) 0.0668(16) Uani 1 1 d . . . . .
H10 H 0.6795 0.3207 0.6296 0.080 Uiso 1 1 calc R . . . .
C11 C 0.5923(6) 0.3397(6) 0.5324(4) 0.0682(16) Uani 1 1 d . . . . .
H11 H 0.5349 0.2867 0.5440 0.082 Uiso 1 1 calc R . . . .
C12 C 0.5874(5) 0.3958(5) 0.4646(3) 0.0611(15) Uani 1 1 d . . . . .
H12 H 0.5266 0.3806 0.4320 0.073 Uiso 1 1 calc R . . . .
C13 C 0.6722(5) 0.4753(5) 0.4436(3) 0.0557(14) Uani 1 1 d . . . . .
C14 C 0.6700(5) 0.5327(6) 0.3699(3) 0.0640(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.339(7) . ?
F2 C14 1.328(7) . ?
F3 C14 1.331(7) . ?
N1 C7 1.318(6) . ?
N1 C8 1.393(7) . ?
N2 H2 0.8600 . ?
N2 C7 1.344(6) . ?
N2 C9 1.393(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.370(9) . ?
C1 C6 1.376(8) . ?
C2 H2A 0.9300 . ?
C2 C3 1.348(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(8) . ?
C6 C7 1.494(8) . ?
C8 C9 1.387(7) . ?
C8 C13 1.416(8) . ?
C9 C10 1.368(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.364(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.399(8) . ?
C13 C14 1.471(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 103.8(4) . . ?
C7 N2 H2 126.3 . . ?
C7 N2 C9 107.3(4) . . ?
C9 N2 H2 126.3 . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.4(6) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 C1 120.7(6) . . ?
C3 C2 H2A 119.6 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.3(6) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(6) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.9(6) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 119.5(6) . . ?
C1 C6 C7 120.2(5) . . ?
C5 C6 C7 120.1(5) . . ?
N1 C7 N2 113.7(5) . . ?
N1 C7 C6 123.8(4) . . ?
N2 C7 C6 122.5(4) . . ?
N1 C8 C13 130.3(5) . . ?
C9 C8 N1 111.0(5) . . ?
C9 C8 C13 118.7(5) . . ?
C8 C9 N2 104.2(5) . . ?
C10 C9 N2 131.9(5) . . ?
C10 C9 C8 123.9(5) . . ?
C9 C10 H10 121.8 . . ?
C11 C10 C9 116.5(6) . . ?
C11 C10 H10 121.8 . . ?
C10 C11 H11 118.6 . . ?
C10 C11 C12 122.7(6) . . ?
C12 C11 H11 118.6 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.2(6) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 C14 121.5(5) . . ?
C12 C13 C8 116.9(5) . . ?
C12 C13 C14 121.6(5) . . ?
F1 C14 C13 113.1(5) . . ?
F2 C14 F1 106.1(6) . . ?
F2 C14 F3 105.4(5) . . ?
F2 C14 C13 113.2(5) . . ?
F3 C14 F1 105.6(5) . . ?
F3 C14 C13 112.8(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C8 C9 N2 1.0(6) . . . . ?
N1 C8 C9 C10 179.4(5) . . . . ?
N1 C8 C13 C12 -179.6(5) . . . . ?
N1 C8 C13 C14 2.3(9) . . . . ?
N2 C9 C10 C11 178.8(6) . . . . ?
C1 C2 C3 C4 2.0(10) . . . . ?
C1 C6 C7 N1 20.2(8) . . . . ?
C1 C6 C7 N2 -158.4(5) . . . . ?
C2 C1 C6 C5 0.2(8) . . . . ?
C2 C1 C6 C7 176.3(5) . . . . ?
C2 C3 C4 C5 -2.3(10) . . . . ?
C3 C4 C5 C6 1.6(10) . . . . ?
C4 C5 C6 C1 -0.5(8) . . . . ?
C4 C5 C6 C7 -176.6(5) . . . . ?
C5 C6 C7 N1 -163.7(5) . . . . ?
C5 C6 C7 N2 17.7(8) . . . . ?
C6 C1 C2 C3 -0.9(9) . . . . ?
C7 N1 C8 C9 -1.7(6) . . . . ?
C7 N1 C8 C13 178.1(6) . . . . ?
C7 N2 C9 C8 0.1(6) . . . . ?
C7 N2 C9 C10 -178.1(6) . . . . ?
C8 N1 C7 N2 1.8(6) . . . . ?
C8 N1 C7 C6 -176.9(5) . . . . ?
C8 C9 C10 C11 0.8(9) . . . . ?
C8 C13 C14 F1 -179.0(5) . . . . ?
C8 C13 C14 F2 -58.3(7) . . . . ?
C8 C13 C14 F3 61.3(7) . . . . ?
C9 N2 C7 N1 -1.3(6) . . . . ?
C9 N2 C7 C6 177.4(5) . . . . ?
C9 C8 C13 C12 0.1(8) . . . . ?
C9 C8 C13 C14 -178.0(5) . . . . ?
C9 C10 C11 C12 -1.1(9) . . . . ?
C10 C11 C12 C13 0.9(10) . . . . ?
C11 C12 C13 C8 -0.3(8) . . . . ?
C11 C12 C13 C14 177.7(6) . . . . ?
C12 C13 C14 F1 3.1(9) . . . . ?
C12 C13 C14 F2 123.7(6) . . . . ?
C12 C13 C14 F3 -116.7(6) . . . . ?
C13 C8 C9 N2 -178.8(5) . . . . ?
C13 C8 C9 C10 -0.4(8) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.617
_oxdiff_exptl_absorpt_empirical_full_min 0.737
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_151030gao
_audit_block_doi                 10.5517/ccdc.csd.cc1mwldh
_database_code_depnum_ccdc_archive 'CCDC 1516067'
_audit_update_record             
;
2016-11-10 deposited with the CCDC.
2016-12-12 downloaded from the CCDC.
;
_audit_creation_date             2015-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H7 F3 N2'
_chemical_formula_sum            'C9 H7 F3 N2'
_chemical_formula_weight         200.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   12.8186(10)
_cell_length_b                   6.8399(6)
_cell_length_c                   9.8413(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     862.87(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    648
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.5060
_cell_measurement_theta_min      3.7860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2301
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.344
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         3.178
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  -7.00   1.00    1.00    --  -19.74 -57.00  30.00   37
  2  ω     49.00  77.00   1.00    1.00    --   18.81-178.00  90.00   28
  3  ω    -10.00  15.00   1.00    1.00    --   18.81  77.00  90.00   25
  4  ω     60.00  88.00   1.00    1.00    --   18.81  77.00  90.00   28
  5  ω     41.00  95.00   1.00    1.00    --   18.81 178.00 -60.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0147330000
_diffrn_orient_matrix_UB_12      0.0225031000
_diffrn_orient_matrix_UB_13      -0.0678189000
_diffrn_orient_matrix_UB_21      0.0037805000
_diffrn_orient_matrix_UB_22      0.1003689000
_diffrn_orient_matrix_UB_23      0.0173528000
_diffrn_orient_matrix_UB_31      0.0531315000
_diffrn_orient_matrix_UB_32      -0.0133840000
_diffrn_orient_matrix_UB_33      0.0174395000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                590
_reflns_number_total             864
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         864
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0562P)²+0.2587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1361
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H9A(0.5) H9B(0.5) H9C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C4(H4), C8(H8)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5240(2) 0.7500 0.9320(2) 0.1029(10) Uani 1 2 d S T P . .
F2 F 0.38731(16) 0.5963(3) 0.87383(18) 0.1036(8) Uani 1 1 d . . . . .
N2 N 0.3537(2) 0.7500 0.3820(3) 0.0538(8) Uani 1 2 d S T P . .
N1 N 0.3002(2) 0.7500 0.5994(3) 0.0579(8) Uani 1 2 d S T P . .
C7 C 0.4079(2) 0.7500 0.5938(3) 0.0425(7) Uani 1 2 d S T P . .
C6 C 0.4428(2) 0.7500 0.4597(3) 0.0429(7) Uani 1 2 d S T P . .
C2 C 0.4815(2) 0.7500 0.6995(3) 0.0428(8) Uani 1 2 d S T P . .
C3 C 0.5865(2) 0.7500 0.6667(4) 0.0481(8) Uani 1 2 d S T P . .
H3 H 0.6363 0.7500 0.7354 0.058 Uiso 1 2 calc RS T P . .
C5 C 0.5482(3) 0.7500 0.4256(4) 0.0505(8) Uani 1 2 d S T P . .
H5 H 0.5702 0.7500 0.3355 0.061 Uiso 1 2 calc RS T P . .
C4 C 0.6178(3) 0.7500 0.5307(4) 0.0535(9) Uani 1 2 d S T P . .
H4 H 0.6888 0.7500 0.5110 0.064 Uiso 1 2 calc RS T P . .
C8 C 0.2731(3) 0.7500 0.4706(4) 0.0624(10) Uani 1 2 d S T P . .
H8 H 0.2038 0.7500 0.4426 0.075 Uiso 1 2 calc RS T P . .
C1 C 0.4464(3) 0.7500 0.8426(4) 0.0609(10) Uani 1 2 d S T P . .
C9 C 0.3463(3) 0.7500 0.2344(4) 0.0749(12) Uani 1 2 d S T P . .
H9A H 0.4068 0.8125 0.1966 0.112 Uiso 0.5 1 calc GR . . A -1
H9B H 0.2848 0.8198 0.2070 0.112 Uiso 0.5 1 calc GR . . A -1
H9C H 0.3424 0.6177 0.2021 0.112 Uiso 0.5 1 calc GR . . A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.329(4) . ?
F2 C1 1.331(3) . ?
N2 C6 1.373(4) . ?
N2 C8 1.352(4) . ?
N2 C9 1.456(5) . ?
N1 C7 1.382(4) . ?
N1 C8 1.314(4) . ?
C7 C6 1.394(4) . ?
C7 C2 1.403(4) . ?
C6 C5 1.393(4) . ?
C2 C3 1.384(4) . ?
C2 C1 1.479(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.397(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.366(5) . ?
C4 H4 0.9300 . ?
C8 H8 0.9300 . ?
C1 F2 1.331(3) 7_575 ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N2 C9 127.5(3) . . ?
C8 N2 C6 106.1(3) . . ?
C8 N2 C9 126.4(3) . . ?
C8 N1 C7 103.1(3) . . ?
N1 C7 C6 110.9(3) . . ?
N1 C7 C2 129.9(3) . . ?
C6 C7 C2 119.1(3) . . ?
N2 C6 C7 105.1(3) . . ?
N2 C6 C5 132.3(3) . . ?
C5 C6 C7 122.6(3) . . ?
C7 C2 C1 120.1(3) . . ?
C3 C2 C7 118.7(3) . . ?
C3 C2 C1 121.2(3) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C6 C5 H5 121.6 . . ?
C4 C5 C6 116.9(3) . . ?
C4 C5 H5 121.6 . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.5(3) . . ?
C5 C4 H4 118.7 . . ?
N2 C8 H8 122.6 . . ?
N1 C8 N2 114.8(3) . . ?
N1 C8 H8 122.6 . . ?
F1 C1 F2 105.8(2) . 7_575 ?
F1 C1 F2 105.8(2) . . ?
F1 C1 C2 113.7(3) . . ?
F2 C1 F2 104.3(3) 7_575 . ?
F2 C1 C2 113.1(2) 7_575 . ?
F2 C1 C2 113.1(2) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C6 C5 C4 180.000(1) . . . . ?
N1 C7 C6 N2 0.000(0) . . . . ?
N1 C7 C6 C5 180.000(0) . . . . ?
N1 C7 C2 C3 180.000(1) . . . . ?
N1 C7 C2 C1 0.000(1) . . . . ?
C7 N1 C8 N2 0.000(0) . . . . ?
C7 C6 C5 C4 0.000(1) . . . . ?
C7 C2 C3 C4 0.000(1) . . . . ?
C7 C2 C1 F1 180.000(1) . . . . ?
C7 C2 C1 F2 59.2(2) . . . . ?
C7 C2 C1 F2 -59.2(2) . . . 7_575 ?
C6 N2 C8 N1 0.000(0) . . . . ?
C6 C7 C2 C3 0.000(1) . . . . ?
C6 C7 C2 C1 180.000(1) . . . . ?
C6 C5 C4 C3 0.000(1) . . . . ?
C2 C7 C6 N2 180.000(0) . . . . ?
C2 C7 C6 C5 0.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C3 C2 C1 F1 0.000(1) . . . . ?
C3 C2 C1 F2 -120.8(2) . . . . ?
C3 C2 C1 F2 120.8(2) . . . 7_575 ?
C8 N2 C6 C7 0.000(0) . . . . ?
C8 N2 C6 C5 180.000(0) . . . . ?
C8 N1 C7 C6 0.000(0) . . . . ?
C8 N1 C7 C2 180.000(1) . . . . ?
C1 C2 C3 C4 180.000(1) . . . . ?
C9 N2 C6 C7 180.000(0) . . . . ?
C9 N2 C6 C5 0.000(1) . . . . ?
C9 N2 C8 N1 180.000(0) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.126
_oxdiff_exptl_absorpt_empirical_full_min 0.904
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_glgao
_audit_block_doi                 10.5517/ccdc.csd.cc1mwlfj
_database_code_depnum_ccdc_archive 'CCDC 1516068'
_audit_update_record             
;
2016-11-10 deposited with the CCDC.
2016-12-12 downloaded from the CCDC.
;
_audit_creation_date             2016-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H11 F3 N2'
_chemical_formula_sum            'C15 H11 F3 N2'
_chemical_formula_weight         276.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N F O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7224(7)
_cell_length_b                   11.5982(5)
_cell_length_c                   11.6209(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.780(6)
_cell_angle_gamma                90
_cell_volume                     1308.87(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1112
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.9340
_cell_measurement_theta_min      3.5010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5040
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_min         3.195
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     60.00  97.00   1.00   40.00    --   18.81-178.00  30.00   37
  2  ω    -51.00  74.00   1.00   40.00    --   18.81   0.00  30.00  125
  3  ω    -47.00  19.00   1.00   40.00    --   18.81 -57.00   0.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0162471000
_diffrn_orient_matrix_UB_12      -0.0068573000
_diffrn_orient_matrix_UB_13      -0.0597987000
_diffrn_orient_matrix_UB_21      0.0669277000
_diffrn_orient_matrix_UB_22      0.0192002000
_diffrn_orient_matrix_UB_23      -0.0123570000
_diffrn_orient_matrix_UB_31      0.0242171000
_diffrn_orient_matrix_UB_32      -0.0576606000
_diffrn_orient_matrix_UB_33      0.0030012000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1355
_reflns_number_total             2380
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0558
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²+0.0801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1442
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5423(2) -0.37818(14) 0.0219(2) 0.1114(9) Uani 1 1 d . . . . .
F2 F 0.7063(2) -0.38863(13) 0.14591(18) 0.0876(7) Uani 1 1 d . . . . .
F3 F 0.7415(3) -0.42589(14) -0.02766(19) 0.1148(9) Uani 1 1 d . . . . .
N1 N 0.6069(2) 0.03298(17) 0.1409(2) 0.0510(6) Uani 1 1 d . . . . .
N2 N 0.5570(2) -0.15347(19) 0.1719(2) 0.0585(7) Uani 1 1 d . . . . .
C1 C 0.5354(3) -0.0459(2) 0.2003(3) 0.0619(9) Uani 1 1 d . . . . .
H1 H 0.4756 -0.0252 0.2569 0.074 Uiso 1 1 calc R . . . .
C2 C 0.6489(3) -0.1451(2) 0.0857(2) 0.0420(6) Uani 1 1 d . . . . .
C3 C 0.6818(3) -0.0299(2) 0.0649(2) 0.0442(7) Uani 1 1 d . . . . .
C4 C 0.7715(3) 0.0030(2) -0.0181(2) 0.0595(8) Uani 1 1 d . . . . .
H4 H 0.7923 0.0802 -0.0304 0.071 Uiso 1 1 calc R . . . .
C5 C 0.8279(4) -0.0825(3) -0.0811(3) 0.0706(10) Uani 1 1 d . . . . .
H5 H 0.8893 -0.0635 -0.1369 0.085 Uiso 1 1 calc R . . . .
C6 C 0.7950(3) -0.1986(2) -0.0632(2) 0.0617(9) Uani 1 1 d . . . . .
H6 H 0.8337 -0.2548 -0.1088 0.074 Uiso 1 1 calc R . . . .
C7 C 0.7076(3) -0.2316(2) 0.0196(2) 0.0464(7) Uani 1 1 d . . . . .
C8 C 0.6755(4) -0.3541(2) 0.0389(3) 0.0642(9) Uani 1 1 d . . . . .
C9 C 0.6028(3) 0.1577(2) 0.1509(3) 0.0609(9) Uani 1 1 d . . . . .
H9A H 0.5299 0.1789 0.2009 0.073 Uiso 1 1 calc R . . . .
H9B H 0.5805 0.1905 0.0755 0.073 Uiso 1 1 calc R . . . .
C10 C 0.7368(3) 0.2094(2) 0.1982(2) 0.0476(7) Uani 1 1 d . . . . .
C11 C 0.8087(3) 0.1618(2) 0.2914(3) 0.0677(9) Uani 1 1 d . . . . .
H11 H 0.7768 0.0945 0.3246 0.081 Uiso 1 1 calc R . . . .
C12 C 0.9282(4) 0.2134(3) 0.3360(3) 0.0777(10) Uani 1 1 d . . . . .
H12 H 0.9762 0.1803 0.3988 0.093 Uiso 1 1 calc R . . . .
C13 C 0.9761(3) 0.3121(3) 0.2887(3) 0.0681(9) Uani 1 1 d . . . . .
H13 H 1.0562 0.3465 0.3193 0.082 Uiso 1 1 calc R . . . .
C14 C 0.9061(3) 0.3601(2) 0.1967(3) 0.0669(9) Uani 1 1 d . . . . .
H14 H 0.9385 0.4274 0.1640 0.080 Uiso 1 1 calc R . . . .
C15 C 0.7860(3) 0.3086(2) 0.1512(3) 0.0609(8) Uani 1 1 d . . . . .
H15 H 0.7387 0.3420 0.0882 0.073 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C8 1.330(4) . ?
F2 C8 1.327(3) . ?
F3 C8 1.323(3) . ?
N1 C1 1.359(3) . ?
N1 C3 1.380(3) . ?
N1 C9 1.452(3) . ?
N2 C1 1.310(3) . ?
N2 C2 1.378(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.397(3) . ?
C2 C7 1.402(3) . ?
C3 C4 1.385(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.368(4) . ?
C7 C8 1.475(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.513(4) . ?
C10 C11 1.376(4) . ?
C10 C15 1.370(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.362(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.358(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(4) . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 105.5(2) . . ?
C1 N1 C9 127.9(2) . . ?
C3 N1 C9 126.5(2) . . ?
C1 N2 C2 103.5(2) . . ?
N1 C1 H1 122.6 . . ?
N2 C1 N1 114.9(2) . . ?
N2 C1 H1 122.6 . . ?
N2 C2 C3 110.8(2) . . ?
N2 C2 C7 130.1(2) . . ?
C3 C2 C7 119.1(2) . . ?
N1 C3 C2 105.2(2) . . ?
N1 C3 C4 132.0(2) . . ?
C4 C3 C2 122.8(2) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.1(2) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.7(3) . . ?
C7 C6 H6 119.1 . . ?
C2 C7 C8 120.7(3) . . ?
C6 C7 C2 118.0(2) . . ?
C6 C7 C8 121.3(2) . . ?
F1 C8 C7 113.0(3) . . ?
F2 C8 F1 104.5(3) . . ?
F2 C8 C7 113.2(3) . . ?
F3 C8 F1 106.1(3) . . ?
F3 C8 F2 105.3(2) . . ?
F3 C8 C7 113.9(3) . . ?
N1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
N1 C9 C10 113.4(2) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C11 C10 C9 121.5(3) . . ?
C15 C10 C9 120.0(3) . . ?
C15 C10 C11 118.5(3) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.7(3) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C4 C5 -179.0(3) . . . . ?
N1 C9 C10 C11 -44.4(4) . . . . ?
N1 C9 C10 C15 138.5(3) . . . . ?
N2 C2 C3 N1 -0.1(3) . . . . ?
N2 C2 C3 C4 -179.6(3) . . . . ?
N2 C2 C7 C6 178.6(3) . . . . ?
N2 C2 C7 C8 -1.2(5) . . . . ?
C1 N1 C3 C2 -0.3(3) . . . . ?
C1 N1 C3 C4 179.1(3) . . . . ?
C1 N1 C9 C10 113.7(3) . . . . ?
C1 N2 C2 C3 0.5(3) . . . . ?
C1 N2 C2 C7 -178.3(3) . . . . ?
C2 N2 C1 N1 -0.7(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C2 C7 C8 F1 60.6(4) . . . . ?
C2 C7 C8 F2 -57.9(4) . . . . ?
C2 C7 C8 F3 -178.2(3) . . . . ?
C3 N1 C1 N2 0.7(3) . . . . ?
C3 N1 C9 C10 -68.8(4) . . . . ?
C3 C2 C7 C6 -0.1(4) . . . . ?
C3 C2 C7 C8 -180.0(3) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 C7 -1.5(5) . . . . ?
C5 C6 C7 C2 1.1(4) . . . . ?
C5 C6 C7 C8 -179.0(3) . . . . ?
C6 C7 C8 F1 -119.2(3) . . . . ?
C6 C7 C8 F2 122.2(3) . . . . ?
C6 C7 C8 F3 2.0(4) . . . . ?
C7 C2 C3 N1 178.8(2) . . . . ?
C7 C2 C3 C4 -0.6(4) . . . . ?
C9 N1 C1 N2 178.6(2) . . . . ?
C9 N1 C3 C2 -178.3(2) . . . . ?
C9 N1 C3 C4 1.1(5) . . . . ?
C9 C10 C11 C12 -177.4(3) . . . . ?
C9 C10 C15 C14 177.3(3) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C11 C10 C15 C14 0.0(4) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C10 0.0(5) . . . . ?
C15 C10 C11 C12 -0.1(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-04-25
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.141
_oxdiff_exptl_absorpt_empirical_full_min 0.880
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ggl20160418-1
_audit_block_doi                 10.5517/ccdc.csd.cc1mwlgk
_database_code_depnum_ccdc_archive 'CCDC 1516069'
_audit_update_record             
;
2016-11-10 deposited with the CCDC.
2016-12-12 downloaded from the CCDC.
;
_audit_creation_date             2016-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 F3 N2 O2'
_chemical_formula_sum            'C12 H11 F3 N2 O2'
_chemical_formula_weight         272.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2208(7)
_cell_length_b                   9.3833(13)
_cell_length_c                   9.5826(11)
_cell_angle_alpha                102.706(11)
_cell_angle_beta                 105.918(10)
_cell_angle_gamma                97.358(10)
_cell_volume                     596.67(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1549
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4560
_cell_measurement_theta_min      3.3650
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3924
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.348
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.995
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      9.00  67.00   1.00    1.00    --   18.81  37.00  60.00   58
  2  ω      8.00  88.00   1.00    1.00    --   18.81  57.00 -30.00   80
  3  ω    -11.00  16.00   1.00    1.00    --  -19.74 -94.00 -37.00   27
  4  ω    -29.00  40.00   1.00    1.00    --   18.81 -57.00  60.00   69
  5  ω    -34.00  39.00   1.00    1.00    --   18.81 -57.00-150.00   73
  6  ω    -20.00  60.00   1.00    1.00    --   18.81 -99.00-180.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0034559000
_diffrn_orient_matrix_UB_12      0.0699042000
_diffrn_orient_matrix_UB_13      -0.0164275000
_diffrn_orient_matrix_UB_21      0.1032125000
_diffrn_orient_matrix_UB_22      0.0224960000
_diffrn_orient_matrix_UB_23      0.0344784000
_diffrn_orient_matrix_UB_31      0.0144184000
_diffrn_orient_matrix_UB_32      -0.0293996000
_diffrn_orient_matrix_UB_33      -0.0701596000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1642
_reflns_number_total             2172
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.094(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²+0.2080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1590
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1698(3) -0.36622(19) 0.6141(3) 0.0971(7) Uani 1 1 d . . . . .
F2 F 0.4722(3) -0.3145(2) 0.6446(2) 0.0883(7) Uani 1 1 d . . . . .
F3 F 0.2769(4) -0.4399(2) 0.4335(2) 0.0985(7) Uani 1 1 d . . . . .
O1 O 0.2214(3) 0.1978(2) 1.0167(2) 0.0608(5) Uani 1 1 d . . . . .
O2 O 0.2571(4) 0.4454(3) 1.0656(3) 0.0872(8) Uani 1 1 d . . . . .
N1 N 0.3042(3) 0.1868(2) 0.7005(2) 0.0462(5) Uani 1 1 d . . . . .
N2 N 0.3485(3) -0.0231(2) 0.7682(2) 0.0452(5) Uani 1 1 d . . . . .
C1 C 0.2987(4) -0.3244(3) 0.5488(3) 0.0553(7) Uani 1 1 d . . . . .
C2 C 0.2713(3) -0.1846(3) 0.5044(3) 0.0454(6) Uani 1 1 d . . . . .
C3 C 0.2175(4) -0.1820(3) 0.3552(3) 0.0566(7) Uani 1 1 d . . . . .
H3 H 0.2009 -0.2692 0.2806 0.068 Uiso 1 1 calc R . . . .
C4 C 0.1876(4) -0.0508(3) 0.3146(3) 0.0622(8) Uani 1 1 d . . . . .
H4 H 0.1524 -0.0522 0.2133 0.075 Uiso 1 1 calc R . . . .
C5 C 0.2088(4) 0.0793(3) 0.4195(3) 0.0572(7) Uani 1 1 d . . . . .
H5 H 0.1859 0.1660 0.3918 0.069 Uiso 1 1 calc R . . . .
C6 C 0.2658(3) 0.0774(3) 0.5691(3) 0.0442(6) Uani 1 1 d . . . . .
C7 C 0.2954(3) -0.0524(3) 0.6138(3) 0.0416(6) Uani 1 1 d . . . . .
C8 C 0.3526(3) 0.1205(3) 0.8150(3) 0.0445(6) Uani 1 1 d . . . . .
C9 C 0.2967(4) 0.3427(3) 0.7096(3) 0.0634(8) Uani 1 1 d . . . . .
H9A H 0.4015 0.3870 0.6794 0.095 Uiso 1 1 calc GR . . . .
H9B H 0.3108 0.3947 0.8113 0.095 Uiso 1 1 calc GR . . . .
H9C H 0.1728 0.3493 0.6441 0.095 Uiso 1 1 calc GR . . . .
C10 C 0.4016(4) 0.2014(3) 0.9765(3) 0.0545(7) Uani 1 1 d . . . . .
H10A H 0.4909 0.1546 1.0386 0.065 Uiso 1 1 calc R . . . .
H10B H 0.4656 0.3039 0.9935 0.065 Uiso 1 1 calc R . . . .
C11 C 0.1671(4) 0.3274(4) 1.0600(3) 0.0624(7) Uani 1 1 d . . . . .
C12 C -0.0165(5) 0.3036(4) 1.0993(4) 0.0867(11) Uani 1 1 d . . . . .
H12A H 0.0114 0.3435 1.2058 0.130 Uiso 1 1 calc GR . . . .
H12B H -0.0706 0.1987 1.0717 0.130 Uiso 1 1 calc GR . . . .
H12C H -0.1093 0.3530 1.0461 0.130 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.321(3) . ?
F2 C1 1.313(3) . ?
F3 C1 1.325(3) . ?
O1 C10 1.453(3) . ?
O1 C11 1.339(3) . ?
O2 C11 1.193(4) . ?
N1 C6 1.372(3) . ?
N1 C8 1.363(3) . ?
N1 C9 1.455(3) . ?
N2 C7 1.376(3) . ?
N2 C8 1.317(3) . ?
C1 C2 1.486(4) . ?
C2 C3 1.381(3) . ?
C2 C7 1.393(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.361(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C6 C7 1.399(3) . ?
C8 C10 1.487(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.478(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C10 118.2(2) . . ?
C6 N1 C9 124.8(2) . . ?
C8 N1 C6 106.63(19) . . ?
C8 N1 C9 128.6(2) . . ?
C8 N2 C7 104.46(19) . . ?
F1 C1 F3 105.2(2) . . ?
F1 C1 C2 112.2(2) . . ?
F2 C1 F1 105.7(2) . . ?
F2 C1 F3 105.9(2) . . ?
F2 C1 C2 113.7(2) . . ?
F3 C1 C2 113.4(2) . . ?
C3 C2 C1 121.6(2) . . ?
C3 C2 C7 118.3(2) . . ?
C7 C2 C1 120.1(2) . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 121.4 . . ?
C4 C5 C6 117.3(3) . . ?
C6 C5 H5 121.4 . . ?
N1 C6 C5 132.3(2) . . ?
N1 C6 C7 105.2(2) . . ?
C5 C6 C7 122.6(2) . . ?
N2 C7 C2 130.5(2) . . ?
N2 C7 C6 110.4(2) . . ?
C2 C7 C6 119.1(2) . . ?
N1 C8 C10 123.4(2) . . ?
N2 C8 N1 113.3(2) . . ?
N2 C8 C10 123.3(2) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C8 108.92(19) . . ?
O1 C10 H10A 109.9 . . ?
O1 C10 H10B 109.9 . . ?
C8 C10 H10A 109.9 . . ?
C8 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O1 C11 C12 111.1(3) . . ?
O2 C11 O1 123.7(3) . . ?
O2 C11 C12 125.3(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C3 -115.6(3) . . . . ?
F1 C1 C2 C7 62.9(3) . . . . ?
F2 C1 C2 C3 124.5(3) . . . . ?
F2 C1 C2 C7 -57.0(3) . . . . ?
F3 C1 C2 C3 3.4(3) . . . . ?
F3 C1 C2 C7 -178.1(2) . . . . ?
N1 C6 C7 N2 0.6(2) . . . . ?
N1 C6 C7 C2 -178.75(19) . . . . ?
N1 C8 C10 O1 88.1(3) . . . . ?
N2 C8 C10 O1 -90.7(3) . . . . ?
C1 C2 C3 C4 178.5(2) . . . . ?
C1 C2 C7 N2 1.9(4) . . . . ?
C1 C2 C7 C6 -179.0(2) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C2 C7 N2 -179.6(2) . . . . ?
C3 C2 C7 C6 -0.4(3) . . . . ?
C3 C4 C5 C6 1.5(4) . . . . ?
C4 C5 C6 N1 178.3(2) . . . . ?
C4 C5 C6 C7 -2.0(4) . . . . ?
C5 C6 C7 N2 -179.2(2) . . . . ?
C5 C6 C7 C2 1.5(3) . . . . ?
C6 N1 C8 N2 0.0(3) . . . . ?
C6 N1 C8 C10 -179.0(2) . . . . ?
C7 N2 C8 N1 0.4(3) . . . . ?
C7 N2 C8 C10 179.3(2) . . . . ?
C7 C2 C3 C4 -0.1(4) . . . . ?
C8 N1 C6 C5 179.4(2) . . . . ?
C8 N1 C6 C7 -0.3(2) . . . . ?
C8 N2 C7 C2 178.6(2) . . . . ?
C8 N2 C7 C6 -0.6(2) . . . . ?
C9 N1 C6 C5 -1.9(4) . . . . ?
C9 N1 C6 C7 178.5(2) . . . . ?
C9 N1 C8 N2 -178.8(2) . . . . ?
C9 N1 C8 C10 2.3(4) . . . . ?
C10 O1 C11 O2 1.0(4) . . . . ?
C10 O1 C11 C12 -178.9(2) . . . . ?
C11 O1 C10 C8 -116.8(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-11
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.368
_oxdiff_exptl_absorpt_empirical_full_min 0.586
